RU2523182C2 - Способ получения функционализованных производных гиалуроновой кислоты и образования их гидрогелей - Google Patents
Способ получения функционализованных производных гиалуроновой кислоты и образования их гидрогелей Download PDFInfo
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- RU2523182C2 RU2523182C2 RU2011126353/13A RU2011126353A RU2523182C2 RU 2523182 C2 RU2523182 C2 RU 2523182C2 RU 2011126353/13 A RU2011126353/13 A RU 2011126353/13A RU 2011126353 A RU2011126353 A RU 2011126353A RU 2523182 C2 RU2523182 C2 RU 2523182C2
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- RU
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- Prior art keywords
- hyaluronic acid
- derivative
- group
- functionalization
- derivatives
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 126
- 238000000034 method Methods 0.000 title claims abstract description 64
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- 230000015572 biosynthetic process Effects 0.000 title description 22
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 120
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 120
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
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- 229940079593 drug Drugs 0.000 claims abstract description 10
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 3
- 238000007306 functionalization reaction Methods 0.000 claims description 68
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 46
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 18
- 238000004132 cross linking Methods 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- LJWSDBHOEIBWJY-QMMMGPOBSA-N (2r)-2-benzamido-3-sulfanylpropanoic acid Chemical group OC(=O)[C@H](CS)NC(=O)C1=CC=CC=C1 LJWSDBHOEIBWJY-QMMMGPOBSA-N 0.000 claims description 12
- 239000012736 aqueous medium Substances 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- GUTXMPQWQSOAIY-HOTGVXAUSA-N (2r)-2-benzamido-3-[[(2r)-2-benzamido-2-carboxyethyl]disulfanyl]propanoic acid Chemical compound N([C@@H](CSSC[C@@H](C(=O)O)NC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 GUTXMPQWQSOAIY-HOTGVXAUSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K9/00—Arc welding or cutting
- B23K9/10—Other electric circuits therefor; Protective circuits; Remote controls
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Arc Welding Control (AREA)
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| ITRM2008A000636 | 2008-11-28 | ||
| IT000636A ITRM20080636A1 (it) | 2008-11-28 | 2008-11-28 | Procedimento per la produzione di derivati funzionalizzati dell acido ialuronico e relativi idrogeli. |
| PCT/EP2009/066060 WO2010061005A1 (fr) | 2008-11-28 | 2009-11-30 | Procédé de production de dérivés fonctionnalisés d'acide hyaluronique et formation d'hydrogels à partir de ceux-ci |
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| RU2734419C2 (ru) * | 2015-10-16 | 2020-10-16 | Мерц Фарма Гмбх Унд Ко. Кгаа | Сшиваемые in situ полисахаридные композиции и варианты их применения |
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| FR2861734B1 (fr) | 2003-04-10 | 2006-04-14 | Corneal Ind | Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus |
| EP2818184B1 (fr) | 2007-11-16 | 2018-10-31 | Allergan, Inc. | Compositions Et Procédés De Traitement Du Purpura |
| US8394782B2 (en) | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having increased longevity |
| US8450475B2 (en) | 2008-08-04 | 2013-05-28 | Allergan, Inc. | Hyaluronic acid-based gels including lidocaine |
| AU2009288118B2 (en) | 2008-09-02 | 2014-12-11 | Allergan, Inc. | Threads of hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
| ITRM20080636A1 (it) | 2008-11-28 | 2010-05-29 | Univ Palermo | Procedimento per la produzione di derivati funzionalizzati dell acido ialuronico e relativi idrogeli. |
| CZ2009836A3 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
| CZ302503B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| US20110172180A1 (en) | 2010-01-13 | 2011-07-14 | Allergan Industrie. Sas | Heat stable hyaluronic acid compositions for dermatological use |
| US9114188B2 (en) | 2010-01-13 | 2015-08-25 | Allergan, Industrie, S.A.S. | Stable hydrogel compositions including additives |
| US8586562B2 (en) | 2010-03-12 | 2013-11-19 | Allergan Industrie, Sas | Fluid compositions for improving skin conditions |
| DK2550027T4 (da) | 2010-03-22 | 2019-05-13 | Allergan Inc | Tværbundne polysaccharid- og protein-polysaccharid-hydrogeler til blødvævsforøgelse |
| IT1401498B1 (it) | 2010-07-30 | 2013-07-26 | Mero Srl | Idrogelo a base di acido ialuronico e suo uso in ortopedia |
| US8889123B2 (en) | 2010-08-19 | 2014-11-18 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US9005605B2 (en) | 2010-08-19 | 2015-04-14 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US8883139B2 (en) | 2010-08-19 | 2014-11-11 | Allergan Inc. | Compositions and soft tissue replacement methods |
| CZ304072B6 (cs) * | 2011-04-26 | 2013-09-25 | Contipro Biotech S.R.O. | Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití |
| US20130096081A1 (en) | 2011-06-03 | 2013-04-18 | Allergan, Inc. | Dermal filler compositions |
| US9393263B2 (en) | 2011-06-03 | 2016-07-19 | Allergan, Inc. | Dermal filler compositions including antioxidants |
| US9408797B2 (en) | 2011-06-03 | 2016-08-09 | Allergan, Inc. | Dermal filler compositions for fine line treatment |
| ES2738208T3 (es) | 2011-06-03 | 2020-01-20 | Allergan Ind Sas | Composiciones de relleno dérmico que incluyen antioxidantes |
| US20130244943A1 (en) | 2011-09-06 | 2013-09-19 | Allergan, Inc. | Hyaluronic acid-collagen matrices for dermal filling and volumizing applications |
| US9662422B2 (en) | 2011-09-06 | 2017-05-30 | Allergan, Inc. | Crosslinked hyaluronic acid-collagen gels for improving tissue graft viability and soft tissue augmentation |
| JP5714456B2 (ja) * | 2011-09-07 | 2015-05-07 | 株式会社シード | 重合性ヒアルロン酸誘導体、ならびにその重合体を含むヒアルロン酸ヒドロゲルおよびコンタクトレンズ |
| CZ303879B6 (cs) | 2012-02-28 | 2013-06-05 | Contipro Biotech S.R.O. | Deriváty na bázi kyseliny hyaluronové schopné tvorit hydrogely, zpusob jejich prípravy, hydrogely na bázi techto derivátu, zpusob jejich prípravy a pouzití |
| KR101240518B1 (ko) * | 2012-03-26 | 2013-03-11 | 주식회사 제네웰 | 생체 적합성 고분자를 이용한 이식용 재료 |
| WO2013181566A1 (fr) * | 2012-05-31 | 2013-12-05 | Cornell University | Hydrogels à base de polysaccharide et hydrogels hybrides et précurseurs de ceux-ci, procédés de fabrication desdits hydrogels et utilisations de ceux-ci |
| CZ304512B6 (cs) | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
| CZ304654B6 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| CZ2012843A3 (cs) | 2012-11-27 | 2014-02-05 | Contipro Biotech S.R.O. | Nekonečná vlákna na bázi hyaluronanu, selektivně oxidovaného v poloze 6 N-acetyl-D-glukosaminové části, jejich příprava, použití, nitě, střiže, příze, textilie a způsob jejich úpravy |
| US20140275340A1 (en) * | 2013-03-15 | 2014-09-18 | Lake Region Manufacturing, Inc. d/b/a Lake Region Medical | Modified hyaluronate hydrophilic compositions, coatings and methods |
| KR20160032000A (ko) | 2013-03-15 | 2016-03-23 | 매튜 알. 드레허 | 이미지화 가능한 색전성 마이크로스피어 |
| US9623157B2 (en) | 2013-03-15 | 2017-04-18 | Lake Region Manufacturing, Inc. | Modified hyaluronate hydrophilic compositions, coatings and methods |
| CZ305153B6 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
| CN103910886B (zh) * | 2014-03-24 | 2016-04-06 | 海南大学 | 半胱氨酸功能化的透明质酸结合物及其合成方法以及在可注射原位形成的水凝胶中的应用 |
| CN106488772B (zh) * | 2014-05-07 | 2020-11-27 | 内米西斯有限公司 | 用于乳糜泄的口服酶疗法的甲基丙烯酸透明质酸衍生物的水凝胶 |
| CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
| ES2761558T3 (es) | 2014-09-30 | 2020-05-20 | Allergan Ind Sas | Composiciones de hidrogel estables que incluyen aditivos |
| WO2016128783A1 (fr) | 2015-02-09 | 2016-08-18 | Allergan Industrie Sas | Compositions et méthodes pour améliorer l'apparence de la peau |
| PL3256179T3 (pl) | 2015-02-13 | 2020-05-18 | Allergan Industrie, Sas | Implanty do kształtowania, uwydatniania lub korygowania cech twarzy takich jak broda |
| CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
| CN108136275A (zh) * | 2015-04-29 | 2018-06-08 | 沃特世科技公司 | 用于超临界流体色谱法的包含离子配对键合相的高纯度色谱材料 |
| CZ2015398A3 (cs) | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
| CZ306662B6 (cs) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití |
| CN114010640A (zh) * | 2015-08-19 | 2022-02-08 | 爱荷华大学研究基金会 | 创伤后骨关节炎的预防性治疗 |
| JP7009371B2 (ja) | 2015-12-29 | 2022-01-25 | ガルデルマ エス.エー. | バイオポリマーを脱アセチル化するための方法 |
| CN105770983B (zh) * | 2016-03-14 | 2019-02-19 | 武汉纺织大学 | 一种透明质酸生物粘合剂的制备方法 |
| JP6675247B2 (ja) * | 2016-03-28 | 2020-04-01 | 株式会社シード | フィブロイン−ヒアルロン酸ハイドロゲル複合体 |
| CZ308106B6 (cs) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
| CN106279729A (zh) * | 2016-08-26 | 2017-01-04 | 北京大清生物技术有限公司 | 一种透明质酸交联凝胶及其制备方法与应用 |
| FR3060239A1 (fr) * | 2016-12-14 | 2018-06-15 | Ge Energy Products France Snc | Procede de determination d'un profil de reponse en statisme d'une machine electrique reliee a un reseau electrique |
| JP2018153296A (ja) * | 2017-03-16 | 2018-10-04 | Jsr株式会社 | 不飽和化合物を含有する組成物 |
| CA3055985A1 (fr) | 2017-03-22 | 2018-09-27 | Genentech, Inc. | Compositions de promedicament d'hydrogel d'acide hyaluronique reticule et procedes |
| US10263552B2 (en) * | 2017-08-08 | 2019-04-16 | Rolls-Royce North American Technologies Inc. | Anticipatory control using output shaft speed |
| CN108187130B (zh) * | 2017-09-15 | 2020-08-18 | 海宁侏罗纪生物科技有限公司 | 一种用于生物损伤修复或止血的试剂及其应用 |
| IT201700122135A1 (it) * | 2017-10-26 | 2019-04-26 | Jointherapeutics S R L | Acido ialuronico funzionalizzato o suo derivato nel trattamento di stati infiammatori |
| US20210015967A1 (en) * | 2018-03-23 | 2021-01-21 | Kaohsiung Medical University | Method for preparing hyaluronic acid hydrogel microparticles and use thereof in repairing articular cartilage defects |
| EP3659632A1 (fr) | 2018-11-29 | 2020-06-03 | Nestlé Skin Health SA | Dégradation partielle post-réticulation d'hydrogels d'amide réticulés |
| CN110384822B (zh) * | 2019-08-19 | 2021-11-16 | 江苏人冠医疗科技有限公司 | 眼用粘合封闭胶及其制备方法 |
| CN110433320A (zh) * | 2019-09-12 | 2019-11-12 | 深圳刚华健医疗有限公司 | 一种医用敷料的制备方法 |
| CN112812200B (zh) * | 2019-11-18 | 2023-06-16 | 孛朗孚(杭州)生物科技有限公司 | 巯基改性高分子化合物及其制备方法和用途 |
| JP7730323B2 (ja) | 2019-12-02 | 2025-08-27 | ガルデルマ ホールディング エスエー | 高分子量美容組成物 |
| US11904006B2 (en) | 2019-12-11 | 2024-02-20 | University Of Iowa Research Foundation | Poly(diaminosulfide) particle-based vaccine |
| CN114269813B (zh) * | 2020-06-01 | 2024-01-02 | 株式会社Lg化学 | 制备聚合物微粒的方法,聚合物微粒,使用其的医用组合物、美容组合物、医用制品和美容制品 |
| IT202000028445A1 (it) | 2020-11-25 | 2022-05-25 | Univ Degli Studi Di Palermo | Nanosistema per la diagnosi ed il trattamento fototermico di tumori |
| TR202022151A2 (tr) * | 2020-12-29 | 2022-07-21 | Vsy Biyoteknoloji Ve Ilac Sanayi Anonim Sirketi | Enjekte edi̇lebi̇li̇r fotoçapraz bağli hi̇yaluroni̇k asi̇t hi̇drojeller, bunlarin üreti̇m yöntemi̇ ve osteoartri̇t tedavi̇si̇ i̇çi̇n kullanimi |
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| ITTS20010013A1 (it) * | 2001-06-04 | 2002-12-04 | Ct Ricerche Poly Tec H A R L S | Nuovi derivati di ialuronano. |
| WO2003002125A2 (fr) * | 2001-06-29 | 2003-01-09 | Astion A/S | Combinaison de sucres amines et cysteine ou de derives de cysteine |
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2008
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- 2009-01-30 US US13/131,098 patent/US8858999B2/en active Active
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- 2009-11-30 RU RU2011126353/13A patent/RU2523182C2/ru not_active IP Right Cessation
- 2009-11-30 SI SI200930470T patent/SI2370474T1/sl unknown
- 2009-11-30 WO PCT/EP2009/066060 patent/WO2010061005A1/fr not_active Ceased
- 2009-11-30 PL PL09795949T patent/PL2370474T3/pl unknown
- 2009-11-30 JP JP2011537999A patent/JP5607061B2/ja active Active
- 2009-11-30 MX MX2011005528A patent/MX2011005528A/es active IP Right Grant
- 2009-11-30 CA CA2744892A patent/CA2744892C/fr active Active
- 2009-11-30 EP EP09795949A patent/EP2370474B1/fr active Active
- 2009-11-30 CN CN200980147761.7A patent/CN102227448B/zh active Active
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| RU2197501C2 (ru) * | 1995-11-15 | 2003-01-27 | Сейкагаку Корпорейшн | Фотоотверженный гель на основе сшитой гиалуроновой кислоты и способ его получения |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2734419C2 (ru) * | 2015-10-16 | 2020-10-16 | Мерц Фарма Гмбх Унд Ко. Кгаа | Сшиваемые in situ полисахаридные композиции и варианты их применения |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0920965B1 (pt) | 2019-07-09 |
| ITRM20080636A1 (it) | 2010-05-29 |
| HK1162546A1 (en) | 2012-08-31 |
| ES2397987T3 (es) | 2013-03-12 |
| PL2370474T3 (pl) | 2013-03-29 |
| WO2010061005A1 (fr) | 2010-06-03 |
| CN102227448B (zh) | 2014-04-02 |
| CA2744892A1 (fr) | 2010-06-03 |
| EP2370474B1 (fr) | 2012-10-24 |
| CA2744892C (fr) | 2016-10-25 |
| DK2370474T3 (da) | 2013-01-14 |
| EP2370474A1 (fr) | 2011-10-05 |
| MX2011005528A (es) | 2011-08-17 |
| SI2370474T1 (sl) | 2013-02-28 |
| US9410000B2 (en) | 2016-08-09 |
| JP5607061B2 (ja) | 2014-10-15 |
| RU2011126353A (ru) | 2013-01-10 |
| JP2012510535A (ja) | 2012-05-10 |
| US20110236486A1 (en) | 2011-09-29 |
| US20150183891A1 (en) | 2015-07-02 |
| US8858999B2 (en) | 2014-10-14 |
| BRPI0920965A2 (pt) | 2016-09-06 |
| CN102227448A (zh) | 2011-10-26 |
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